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Jul 16, 2018 · 15m · top-founders

1087 Yeah I'd sell (Live negotiation)

James Kappen · 6m spoken Nathan Latka · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Nathan Latka interviews Proposable founder James Kappen to analyze the software company's $25,000 monthly recurring revenue, customer acquisition tactics, onboarding churn, and the viability of a potential acquisition.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 47.2% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 1.0 Guest disagreement 1.8 Nathan pushing back 4.8
05100:0010:000:49–4:01 · Nathan as informed peer 6/10 Proposable's Market Positioning and Competitor Differentiation Nathan scrutinizes James's differentiation strategy against both all-in-one tools like DocSend and single point solutions like DocuSign, catching James in what appears to be a contradictory value proposition.4:01–9:03 · Nathan as informed peer 6/10 Pricing Model, Origin Story, and Remote Team Nathan rapidly calculates MRR based on seat count and pricing, then aggressively pushes James to disclose the equity percentage taken by his accelerator.9:05–11:52 · Nathan as informed peer 6/10 Sponsor Message: HostGator Website Builder After a brief sponsor ad, Nathan digs into James's flat growth and proposes a hypothetical buyout valuation to let James exit and pursue other projects.11:53–14:53 · Nathan as informed peer 7/10 Customer Churn Analysis and Onboarding Obstacles Nathan presses James on vague churn figures, dispels the notion that any churn is bad, and explains the core distinction between logo churn and revenue churn before running through the Famous Five.14:54–15:26 · Nathan as informed peer 0/10 Episode Summary and Key Takeaways Nathan recaps the company's metrics, origin story, and churn stats in a concluding solo outro summary.0:49–4:01 · Guest teaching 3/10 Proposable's Market Positioning and Competitor Differentiation Nathan scrutinizes James's differentiation strategy against both all-in-one tools like DocSend and single point solutions like DocuSign, catching James in what appears to be a contradictory value proposition.4:01–9:03 · Guest teaching 1/10 Pricing Model, Origin Story, and Remote Team Nathan rapidly calculates MRR based on seat count and pricing, then aggressively pushes James to disclose the equity percentage taken by his accelerator.9:05–11:52 · Guest teaching 1/10 Sponsor Message: HostGator Website Builder After a brief sponsor ad, Nathan digs into James's flat growth and proposes a hypothetical buyout valuation to let James exit and pursue other projects.11:53–14:53 · Guest teaching 0/10 Customer Churn Analysis and Onboarding Obstacles Nathan presses James on vague churn figures, dispels the notion that any churn is bad, and explains the core distinction between logo churn and revenue churn before running through the Famous Five.14:54–15:26 · Guest teaching 0/10 Episode Summary and Key Takeaways Nathan recaps the company's metrics, origin story, and churn stats in a concluding solo outro summary.0:49–4:01 · Guest disagreement 3/10 Proposable's Market Positioning and Competitor Differentiation Nathan scrutinizes James's differentiation strategy against both all-in-one tools like DocSend and single point solutions like DocuSign, catching James in what appears to be a contradictory value proposition.4:01–9:03 · Guest disagreement 2/10 Pricing Model, Origin Story, and Remote Team Nathan rapidly calculates MRR based on seat count and pricing, then aggressively pushes James to disclose the equity percentage taken by his accelerator.9:05–11:52 · Guest disagreement 2/10 Sponsor Message: HostGator Website Builder After a brief sponsor ad, Nathan digs into James's flat growth and proposes a hypothetical buyout valuation to let James exit and pursue other projects.11:53–14:53 · Guest disagreement 2/10 Customer Churn Analysis and Onboarding Obstacles Nathan presses James on vague churn figures, dispels the notion that any churn is bad, and explains the core distinction between logo churn and revenue churn before running through the Famous Five.14:54–15:26 · Guest disagreement 0/10 Episode Summary and Key Takeaways Nathan recaps the company's metrics, origin story, and churn stats in a concluding solo outro summary.0:49–4:01 · Nathan pushing back 7/10 Proposable's Market Positioning and Competitor Differentiation Nathan scrutinizes James's differentiation strategy against both all-in-one tools like DocSend and single point solutions like DocuSign, catching James in what appears to be a contradictory value proposition.4:01–9:03 · Nathan pushing back 6/10 Pricing Model, Origin Story, and Remote Team Nathan rapidly calculates MRR based on seat count and pricing, then aggressively pushes James to disclose the equity percentage taken by his accelerator.9:05–11:52 · Nathan pushing back 5/10 Sponsor Message: HostGator Website Builder After a brief sponsor ad, Nathan digs into James's flat growth and proposes a hypothetical buyout valuation to let James exit and pursue other projects.11:53–14:53 · Nathan pushing back 6/10 Customer Churn Analysis and Onboarding Obstacles Nathan presses James on vague churn figures, dispels the notion that any churn is bad, and explains the core distinction between logo churn and revenue churn before running through the Famous Five.14:54–15:26 · Nathan pushing back 0/10 Episode Summary and Key Takeaways Nathan recaps the company's metrics, origin story, and churn stats in a concluding solo outro summary.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 35.3% · guest 64.7%0:00 · Nathan 35.3% · guest 64.7%3:00 · Nathan 26.4% · guest 73.6%3:00 · Nathan 26.4% · guest 73.6%6:00 · Nathan 46.2% · guest 53.8%6:00 · Nathan 46.2% · guest 53.8%9:00 · Nathan 71.7% · guest 28.3%9:00 · Nathan 71.7% · guest 28.3%12:00 · Nathan 50.3% · guest 49.7%12:00 · Nathan 50.3% · guest 49.7%15:00 · Nathan 99% · guest 1%15:00 · Nathan 99% · guest 1%
Sharpest disagreement ▶ 3:19 Guest defends product positioning against host's binary framing

James directly pushes back against Nathan's dichotomy, insisting that focusing on the proposal workflow inherently bridges both extremes.

 Hardest push from Nathan ▶ 3:08 Host calls out logical contradiction in differentiation pitch

Nathan bluntly corners James on claiming to do only one thing versus DocSend while simultaneously claiming to offer more features than point solutions.

 Biggest teaching moment ▶ 2:29 Guest breaks down the commoditization of e-signatures

James educates Nathan on why standalone e-signatures have become table stakes and why unifying creation, tracking, and signing into a single proposal workflow matters.

 Nathan holds their own ▶ 12:22 Host breaks down churn strategy and defines logo churn

Nathan demonstrates SaaS expertise by correcting James's assumption about churn and explaining how logo churn differs from revenue churn.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Proposable's Market Positioning and Competitor Differentiation 6337 Nathan scrutinizes James's differentiation strategy against both all-in-one tools like DocSend and single point solutions like DocuSign, catching James in what appears to be a contradictory value proposition.
Pricing Model, Origin Story, and Remote Team 6126 Nathan rapidly calculates MRR based on seat count and pricing, then aggressively pushes James to disclose the equity percentage taken by his accelerator.
Sponsor Message: HostGator Website Builder 6125 After a brief sponsor ad, Nathan digs into James's flat growth and proposes a hypothetical buyout valuation to let James exit and pursue other projects.
Customer Churn Analysis and Onboarding Obstacles 7026 Nathan presses James on vague churn figures, dispels the notion that any churn is bad, and explains the core distinction between logo churn and revenue churn before running through the Famous Five.
Episode Summary and Key Takeaways 0000 Nathan recaps the company's metrics, origin story, and churn stats in a concluding solo outro summary.

Statements from this episode (13)

Insight
Kappen: E-signatures are becoming a commodity
“Signatures, e-signatures are becoming a commodity. Everyone does e-signatures now. They're all legal. Most of them are legal. It's kind of the general consensus that e-signing is a legitimate way to sign documents and close deals.”
James Kappen Jul 16, 2018 ▶ 2:35
Assertion Not checkable as stated
Kappen: Proposable customers pay around $50 per seat monthly
“It's higher than that. It's more like 50.”
James Kappen Jul 16, 2018 ▶ 4:32
Assertion Not checkable as stated
Kappen: Proposable operates with a team of five people
“We're still a small team. So we're, it's five of us.”
James Kappen Jul 16, 2018 ▶ 5:37
Assertion Not checkable as stated
Kappen: Proposable has roughly 300 customer companies
“So we're right around 300.”
James Kappen Jul 16, 2018 ▶ 5:52
Assertion Not checkable as stated
Kappen: Proposable counts over 500 active paid seats
“We're right around, we're over 500 active users.”
James Kappen Jul 16, 2018 ▶ 6:53
Disclosure
Kappen: Proposable raised a $250k seed round from Sproutbox
“That was 250 K.”
James Kappen Jul 16, 2018 ▶ 7:41
Disclosure
Sproutbox took 30% equity in Proposable for a $250k seed round
“So they took 30%.”
James Kappen Jul 16, 2018 ▶ 8:29
Assertion Not checkable as stated
Kappen: Proposable revenue was flat year-over-year
“No, I think we were flat. I think last year to this year.”
James Kappen Jul 16, 2018 ▶ 10:07
Disclosure
James Kappen is open to selling Proposable for the right payout
“Yeah, I would be interested.”
James Kappen Jul 16, 2018 ▶ 11:01
Assertion Supported
Kappen: Has spent nine years building Proposable
“I mean, if you take nine, nine years kind of working on then, you know.”
James Kappen Jul 16, 2018 ▶ 11:13
Insight
Latka: Zero churn might indicate a SaaS product is priced too low
“If you have zero churn, it might mean your price point's too low. Nobody's churning. Churn can be a good thing.”
Nathan Latka Jul 16, 2018 ▶ 12:23
Disclosure
Kappen: Proposable experiences 5% to 10% monthly customer logo churn
“We've been between five and 10%.”
James Kappen Jul 16, 2018 ▶ 12:31
Insight
Kappen: Content migration friction drives customer churn for Proposable
“One of the main friction points actually is moving their content from wherever they have it, Microsoft word, Excel, Dropbox, getting it into our platform. And so when people don't quite get their content in It's not as sticky.”
James Kappen Jul 16, 2018 ▶ 13:27
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